Search Holiday Homes in Bailey Island

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Browse Select Bailey Island Holiday Homes

Fridge, microwave, oven, stovetop
Stunning oceanfront cottage w/ private deck and Atlantic views
9.2 out of 10, Wonderful, (37)
"The view was exceptional "
Stunning oceanfront cottage w/ private deck and Atlantic views
Fridge, microwave, oven, stovetop
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
10.0 out of 10, Exceptional, (51)
"Comfortable, clean, very well decorated apartment in a pleasant, walkable neighborhood. I highly recommend this property."
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
Exterior
Rent a room in the gorgeous Holt House
8.4 out of 10, Very good, (19)
"It was a great trip up to Portland and the property met our needs."
Rent a room in the gorgeous Holt House
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Interior
Riverfront Topsham Home ~ 28 Mi to Portland!
Riverfront Topsham Home ~ 28 Mi to Portland!
TV, fireplace
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
8.8 out of 10, Excellent, (33)
"Great views. House pretty clean & supplies were fine except only 3 coffee cups for 6 adults. VACasa said they would get more cups. They failed, never received. Some lights didn't work & lots of dead bugs in light fixtures."
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
Interior
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
8.8 out of 10, Excellent, (48)
"This was a great old townhouse. Great parking and very clean. Easy walk to attractions and a charming neighborhood bar just around the corner. "
The price is £199
includes taxes & fees
14 May - 15 May
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Property grounds
325 Year OldWaterfront Fully Renovated Loaded with Amenities Bring Your Boat!
10.0 out of 10, Exceptional, (20)
"The property and home were very charming, lovely views from every room of the tawny late November marsh landscape. Recent renovations provided creature comforts, and getting out to explore in-town Bath or out to Reid was a short car ride away. Accessibility for older family was great with the single level and low entry thresholds. Tina was great for communicating with- our best wishes!"
325 Year OldWaterfront Fully Renovated Loaded with Amenities Bring Your Boat!
View from property
NEW VRBO LISTING 2 bed/2bath on a beautiful tidal cove with 3 wooded acres
NEW VRBO LISTING 2 bed/2bath on a beautiful tidal cove with 3 wooded acres
Property grounds
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
9.4 out of 10, Exceptional, (19)
"Great location!"
Dog-friendly Fisher Hill home with patio and wood stove - walk to the harbor
Fridge, microwave, oven, stovetop
Dog-friendly home with deck, pool table, & firepit - walk to downtown Boothbay
9.6 out of 10, Exceptional, (26)
"We had a great stay! Close to town and had everything we needed here. Thank you!"
Dog-friendly home with deck, pool table, & firepit - walk to downtown Boothbay
Property grounds
Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, (99)
"Lovely home in a beautiful location. Very welcoming, cozy, and friendly. Easy check-in and check-out process. The owner was very accommodating and helpful. Made amazing memories and look forward to returning soon. Thank you so much!"
Charming 110-year former Inn 10' from the Ocean!
Private kitchen | Fridge, microwave, oven, stovetop
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
9.4 out of 10, Exceptional, (21)
"Stayed for a weekend for bachelorette party! Very clean, close to downtown and loved the hot tub."
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
4 bedrooms, desk, iron/ironing board, WiFi
Cozy, Waterfront Cabin-Style Gem with Private Dock and Lovely Views
8.8 out of 10, Excellent, (43)
"We enjoyed our stay and found the owners provided numerous little helpful extras. The only somewhat significant challenge is the recurring 31 stairs' climb, but the reward is a great view."
Cozy, Waterfront Cabin-Style Gem with Private Dock and Lovely Views
Fridge, microwave, oven, stovetop
Full sized home
9.0 out of 10, Wonderful, (2)
"It was a nice little house"
The price is £281
includes taxes & fees
14 May - 15 May
Full sized home
1 bedroom, Internet, bed sheets
Munjoy Hill hideaway with fireplace & AC - walk to dining & Eastern Promenade
9.2 out of 10, Wonderful, (10)
"We stayed a few nights in November while in town for a wedding. The apartment was just as pictured and described, with extra blankets and such for warming up. I had an issue with the fireplace in the bedroom not coming on. I contacted the property manager who reached out to the owner and someone was there to fix it within an hour. Only other negative was the hot water in the shower didn’t last very long. Otherwise, I’d was very cozy and comfortable, very quiet at night. The apartment is close...
Munjoy Hill hideaway with fireplace & AC - walk to dining & Eastern Promenade
Dining
New home at Popham Beach
10.0 out of 10, Exceptional, (4)
"Wonderful way to decompress and walk the sandy beaches at Popham. The property, the views, our host, and all details were great!"
New home at Popham Beach
Interior
A yurt in the trees. Close to Portland but close to nature. Treeyurt Maine
A yurt in the trees. Close to Portland but close to nature. Treeyurt Maine
Fridge, microwave, oven, stovetop
Spacious property with pool, grill, deck, children's items, & W/D - dog-friendly
Spacious property with pool, grill, deck, children's items, & W/D - dog-friendly
Aerial view
Stover's Cove Beach Coastal Retreat
9.4 out of 10, Exceptional, (28)
"We had a great sray in this lovely home. Close to the water. ..fortunately the neighbor told us how to get down there! Plenty to see and do. Well stocked home."
Stover's Cove Beach Coastal Retreat
Aerial view
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome
8.8 out of 10, Excellent, (43)
"It was so quiet and peaceful. The home was perfect and the back deck made it even better!"
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome
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See all available properties in Bailey Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Bailey Island

Property grounds
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
10.0 out of 10, Exceptional, (94)
"We celebrated our Mom’s 70th birthday in this beautiful space. It exceeded our expectations and the property manager David is the best!"
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Fridge, microwave, oven, stovetop
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Exterior
Completely remodeled 2 bedroom apartment in Portland's West End
10.0 out of 10, Exceptional, (35)
"We very much enjoyed our stay at this location. The stairs were a bit scary, but with the light on, you'll be fine. :) Cozy spot for the three of us, well appointed and in a fantastic area. Very walkable, even down to the wharf. We are from a very non-walkable area, so it was amazing to see all the activity and places we could go just walking a bit. We enjoyed our first time in Maine, and can't wait to get back for a longer trip. Thanks to the hosts!"
The price is £335
includes taxes & fees
19 May - 20 May
Completely remodeled 2 bedroom apartment in Portland's West End
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.